CA2818308A1 - Bifunctional molecules with antibody-recruiting and entry inhibitory activity against the human immunodeficiency virus - Google Patents
Bifunctional molecules with antibody-recruiting and entry inhibitory activity against the human immunodeficiency virus Download PDFInfo
- Publication number
- CA2818308A1 CA2818308A1 CA2818308A CA2818308A CA2818308A1 CA 2818308 A1 CA2818308 A1 CA 2818308A1 CA 2818308 A CA2818308 A CA 2818308A CA 2818308 A CA2818308 A CA 2818308A CA 2818308 A1 CA2818308 A1 CA 2818308A1
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- Prior art keywords
- group
- alkyl
- ch2o
- compound according
- hiv
- Prior art date
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- Abandoned
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- 230000001588 bifunctional effect Effects 0.000 title claims abstract description 57
- 230000002401 inhibitory effect Effects 0.000 title claims abstract description 8
- 241000725303 Human immunodeficiency virus Species 0.000 title description 78
- 150000001875 compounds Chemical class 0.000 claims abstract description 178
- 230000027455 binding Effects 0.000 claims abstract description 40
- 208000031886 HIV Infections Diseases 0.000 claims abstract description 34
- -1 dinitrophenyl Chemical group 0.000 claims description 73
- 125000005647 linker group Chemical group 0.000 claims description 65
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
- 239000000203 mixture Substances 0.000 claims description 50
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 41
- 239000000126 substance Substances 0.000 claims description 35
- 210000004027 cell Anatomy 0.000 claims description 33
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 28
- 229910052801 chlorine Inorganic materials 0.000 claims description 27
- 229910052731 fluorine Inorganic materials 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- 208000037357 HIV infectious disease Diseases 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 25
- 239000008194 pharmaceutical composition Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 17
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
- 229920001223 polyethylene glycol Polymers 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 239000002259 anti human immunodeficiency virus agent Substances 0.000 claims description 12
- 229940124411 anti-hiv antiviral agent Drugs 0.000 claims description 12
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
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- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
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- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
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- 102200009479 rs141772938 Human genes 0.000 description 1
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- 150000003308 rutinuloses Chemical class 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
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- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
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- 230000003381 solubilizing effect Effects 0.000 description 1
- PZDOWFGHCNHPQD-VNNZMYODSA-N sophorose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](C=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O PZDOWFGHCNHPQD-VNNZMYODSA-N 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
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- 229940075582 sorbic acid Drugs 0.000 description 1
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- 229940035048 sorbitan monostearate Drugs 0.000 description 1
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- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
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- 230000002195 synergetic effect Effects 0.000 description 1
- MHXBHWLGRWOABW-UHFFFAOYSA-N tetradecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCC MHXBHWLGRWOABW-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- ONCNIMLKGZSAJT-UHFFFAOYSA-N thieno[3,2-b]furan Chemical compound S1C=CC2=C1C=CO2 ONCNIMLKGZSAJT-UHFFFAOYSA-N 0.000 description 1
- RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
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- 238000011200 topical administration Methods 0.000 description 1
- 229940100611 topical cream Drugs 0.000 description 1
- 229940100617 topical lotion Drugs 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000010415 tropism Effects 0.000 description 1
- RULSWEULPANCDV-PIXUTMIVSA-N turanose Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](C(=O)CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RULSWEULPANCDV-PIXUTMIVSA-N 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
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- 150000003751 zinc Chemical class 0.000 description 1
- AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical compound N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- Dermatology (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41497710P | 2010-11-18 | 2010-11-18 | |
| US61/414,977 | 2010-11-18 | ||
| US201161522518P | 2011-08-11 | 2011-08-11 | |
| US61/522,518 | 2011-08-11 | ||
| PCT/US2011/061174 WO2012068366A2 (en) | 2010-11-18 | 2011-11-17 | Bifunctional molecules with antibody-recruiting and entry inhibitory activity against the human immunodeficiency virus |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2818308A1 true CA2818308A1 (en) | 2012-05-24 |
Family
ID=46084646
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2818308A Abandoned CA2818308A1 (en) | 2010-11-18 | 2011-11-17 | Bifunctional molecules with antibody-recruiting and entry inhibitory activity against the human immunodeficiency virus |
Country Status (16)
| Country | Link |
|---|---|
| US (5) | US9562038B2 (es) |
| EP (1) | EP2640720B1 (es) |
| JP (2) | JP6155193B2 (es) |
| KR (1) | KR20140000275A (es) |
| CN (2) | CN103402998B (es) |
| AU (1) | AU2011329829B2 (es) |
| BR (1) | BR112013012309A2 (es) |
| CA (1) | CA2818308A1 (es) |
| CL (1) | CL2013001429A1 (es) |
| CO (1) | CO6801635A2 (es) |
| EA (1) | EA201390726A1 (es) |
| IL (1) | IL226397B (es) |
| MX (1) | MX350974B (es) |
| PE (1) | PE20140406A1 (es) |
| SG (2) | SG190829A1 (es) |
| WO (1) | WO2012068366A2 (es) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US7371772B2 (en) | 2001-08-08 | 2008-05-13 | Takeda Pharmaceutical Company Limited | Bicyclic compound, production and use thereof |
| WO2011046946A2 (en) * | 2009-10-13 | 2011-04-21 | Yale University | Bifunctional molecules with antibody-recruiting and entry inhibitory activity against the human immunodeficiency virus |
| CN103402998B (zh) | 2010-11-18 | 2017-09-26 | 耶鲁大学 | 具有募集抗体并对人体免疫缺陷病毒进入有抑制活性的双功能分子 |
| WO2013070688A1 (en) | 2011-11-11 | 2013-05-16 | Yale University | Reprogramming urokinase into an antibody-recruiting anticancer agent |
| US9745334B2 (en) | 2012-04-26 | 2017-08-29 | Yale University | Cytotoxic-drug delivering molecules targeting HIV (CDM-Hs), cytotoxic activity against the human immunodeficiency virus and methods of use |
| US9556167B2 (en) | 2012-05-02 | 2017-01-31 | Yale University | TLR-agonist-conjugated antibody recruiting molecules (TLR-ARMs) |
| ES2824026T3 (es) | 2013-05-03 | 2021-05-11 | Univ Yale | Compuestos miméticos de anticuerpos sintéticos (SyAM) dirigidos al cáncer, especialmente cáncer de próstata |
| BR112017013130A2 (pt) | 2014-12-23 | 2017-12-26 | Tobira Therapeutics Inc | processo de fabricação de cenicriviroc e análogos relacionados |
| WO2017023994A1 (en) | 2015-08-06 | 2017-02-09 | Yale University | Small molecule based antibody-recruiting compounds for cancer treatment |
| SG11201804787UA (en) | 2015-12-15 | 2018-07-30 | Gilead Sciences Inc | Human immunodeficiency virus neutralizing antibodies |
| KR102471267B1 (ko) | 2016-03-18 | 2022-11-29 | 럿거스, 더 스테이트 유니버시티 오브 뉴저지 | 생체내 절단가능한 연결 모이어티에 의해 항-매트립타제 항체에 접합되는 화학요법제를 사용하여 종양 세포를 표적화하는 방법 |
| AU2017280068A1 (en) | 2016-06-21 | 2019-01-31 | Tobira Therapeutics, Inc. | Purified cenicriviroc and purified intermediates for making cenicriviroc |
| WO2018026997A1 (en) | 2016-08-03 | 2018-02-08 | Yale University | Antibody-recruiting molecules for the treatment of cancer |
| EP3506896A4 (en) | 2016-08-31 | 2020-08-26 | Tobira Therapeutics, Inc. | SOLID FORMS OF CENICRIVIROC MESYLATE AND METHOD FOR MANUFACTURING SOLID FORMS OF CENICRIVIROC MESYLATE |
| CN107056762B (zh) * | 2016-12-22 | 2020-08-28 | 四川百利药业有限责任公司 | 一种用作抗流感病毒的双羰基类似物 |
| KR102324568B1 (ko) | 2017-06-21 | 2021-11-10 | 길리애드 사이언시즈, 인코포레이티드 | HIV gp120 및 CD3을 표적화하는 다중특이적 항체 |
| WO2021151391A1 (zh) * | 2020-01-30 | 2021-08-05 | 沈阳福洋医药科技有限公司 | 异戊酰螺旋霉素类化合物及其组合物在制备抗病毒药物中的应用 |
| CN111995622B (zh) * | 2020-08-20 | 2022-04-15 | 复旦大学 | 化合物及其用途 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4522811A (en) | 1982-07-08 | 1985-06-11 | Syntex (U.S.A.) Inc. | Serial injection of muramyldipeptides and liposomes enhances the anti-infective activity of muramyldipeptides |
| ZA893284B (en) * | 1988-05-04 | 1990-03-28 | Igen Inc | Peptide analogs and their use as haptens to elicit catalytic antibodies |
| EP1138334A3 (en) * | 1992-06-09 | 2002-04-03 | Neorx Corporation | Pretargeting methods and compounds |
| JP3319073B2 (ja) * | 1993-08-24 | 2002-08-26 | 和光純薬工業株式会社 | 免疫学的測定方法 |
| US6140505A (en) * | 1995-03-10 | 2000-10-31 | G. D. Searle & Co. | Synthesis of benzo fused heterocyclic sulfonyl chlorides |
| US6469006B1 (en) * | 1999-06-15 | 2002-10-22 | Bristol-Myers Squibb Company | Antiviral indoleoxoacetyl piperazine derivatives |
| US6573262B2 (en) * | 2000-07-10 | 2003-06-03 | Bristol-Myers Sqibb Company | Composition and antiviral activity of substituted indoleoxoacetic piperazine derivatives |
| WO2002004440A1 (en) * | 2000-07-10 | 2002-01-17 | Bristol-Myers Squibb Company | Composition and antiviral activity of substituted indoleoxoacetic piperazine derivatives |
| US6825201B2 (en) * | 2001-04-25 | 2004-11-30 | Bristol-Myers Squibb Company | Indole, azaindole and related heterocyclic amidopiperazine derivatives |
| HUP0401523A3 (en) * | 2004-07-29 | 2007-05-02 | Richter Gedeon Vegyeszet | Indole-2-carboxamide derivatives, pharmaceutical compositions containing them and process for producing them |
| ES2493166T3 (es) * | 2006-11-01 | 2014-09-11 | Ventana Medical Systems, Inc. | Haptenos, conjugados de haptenos, composiciones de los mismos y método para su preparación y uso |
| DK2291659T3 (en) * | 2008-05-13 | 2015-12-21 | Univ Yale | SMALL CHEMICAL MOLECULES FOR RECRUITING ANTIBODIES TO CANCER CELLS |
| EP2318051A4 (en) * | 2008-07-14 | 2012-12-26 | Andrew Metters | IN VITRO DIAGNOSTIC MARKERS COMPRISING CARBON NANOPARTICLES AND KITS |
| US8518927B2 (en) * | 2009-02-10 | 2013-08-27 | The Scripps Research Institute | Chemically programmed vaccination |
| WO2011046946A2 (en) * | 2009-10-13 | 2011-04-21 | Yale University | Bifunctional molecules with antibody-recruiting and entry inhibitory activity against the human immunodeficiency virus |
| US8450361B2 (en) * | 2010-08-06 | 2013-05-28 | Bristol-Myers Squibb Company | Substituted indole and azaindole oxoacetyl piperazinamide derivatives |
| CN103402998B (zh) * | 2010-11-18 | 2017-09-26 | 耶鲁大学 | 具有募集抗体并对人体免疫缺陷病毒进入有抑制活性的双功能分子 |
-
2011
- 2011-11-17 CN CN201180065404.3A patent/CN103402998B/zh active Active
- 2011-11-17 EP EP11842404.3A patent/EP2640720B1/en active Active
- 2011-11-17 JP JP2013540011A patent/JP6155193B2/ja active Active
- 2011-11-17 EA EA201390726A patent/EA201390726A1/ru unknown
- 2011-11-17 SG SG2013038344A patent/SG190829A1/en unknown
- 2011-11-17 MX MX2013005462A patent/MX350974B/es active IP Right Grant
- 2011-11-17 PE PE2013001206A patent/PE20140406A1/es not_active Application Discontinuation
- 2011-11-17 US US13/988,251 patent/US9562038B2/en active Active
- 2011-11-17 WO PCT/US2011/061174 patent/WO2012068366A2/en active Application Filing
- 2011-11-17 CN CN201611167953.2A patent/CN107011333B/zh active Active
- 2011-11-17 KR KR1020137015098A patent/KR20140000275A/ko not_active Application Discontinuation
- 2011-11-17 AU AU2011329829A patent/AU2011329829B2/en active Active
- 2011-11-17 CA CA2818308A patent/CA2818308A1/en not_active Abandoned
- 2011-11-17 SG SG10201510402WA patent/SG10201510402WA/en unknown
- 2011-11-17 BR BR112013012309A patent/BR112013012309A2/pt not_active Application Discontinuation
-
2013
- 2013-05-16 IL IL226397A patent/IL226397B/en active IP Right Grant
- 2013-05-17 CL CL2013001429A patent/CL2013001429A1/es unknown
- 2013-06-07 CO CO13138546A patent/CO6801635A2/es not_active Application Discontinuation
-
2016
- 2016-11-04 JP JP2016215788A patent/JP6567486B2/ja active Active
- 2016-12-15 US US15/379,969 patent/US10030008B2/en active Active
-
2018
- 2018-07-17 US US16/037,678 patent/US10703743B2/en active Active
-
2020
- 2020-06-05 US US16/894,362 patent/US11136316B2/en active Active
-
2021
- 2021-09-09 US US17/470,393 patent/US11858917B2/en active Active
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| Date | Code | Title | Description |
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| EEER | Examination request |
Effective date: 20161116 |
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| FZDE | Discontinued |
Effective date: 20190613 |